Benzonitrile, 4-bromo- → 4-(2-Cyanoethyl)benzonitrile

HRID 920867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 920867
C([O-])(=O)C(C)(C)C.[C:8]([CH2:10][CH2:11][Zn+])#[N:9].Br[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1.[NH4+].[Cl-]>C1COCC1.CN1C(=O)CCC1>[C:8]([CH2:10][CH2:11][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1)#[N:9]

Komponenten

6

Edukt 3

HCID 12162Benzonitrile, 4-bromo-HCID 25517Ammonium ChlorideHCID 178447613HCID 178447613, Verbindung

Produkt 1

HCID 2730084-(2-Cyanoethyl)benzonitrileAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

In a dry and argon-flushed Schlenk-flask, equipped with a magnetic stirring bar and a septum, (2-cyanoethyl)zinc pivalate (1t) (2.35 g, 2150 mg/mmol, 1.09 mmol) was dissolved in a mixture of THF (3.0 mL) and NMP (1.0 mL). 4-Bromobenzonitrile (168 mg, 0.92 mmol) was added followed by PEPPSI-iPr (14 mg, 0.02 mmol) and the mixture was stirred for 12 h at 50° C. Then sat. aq. NH4Cl (10 mL) was added and the aqueous layer was extracted with EtOAc (3×20 mL). The combined organic phases were dried (Na2SO4). Evaporation of the solvents in vacuo and purification by flash chromatography (silica gel, ihexane/Et2O=3:1) afforded 4-(2-cyanoethyl)benzonitrile (entry 26) (113 mg, 80%) as a pale yellow oil.

Aufarbeitung

  1. customIn a dry
  2. customargon-flushed Schlenk-flask
  3. customequipped with a magnetic stirring bar
  4. extractionthe aqueous layer was extracted with EtOAc (3×20 mL)
  5. dry with materialThe combined organic phases were dried (Na2SO4)
  6. customEvaporation of the solvents
  7. customin vacuo and purification by flash chromatography (silica gel, ihexane/Et2O=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-0f140fb7efe24bf7b1bf5fca4012625e
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273070B2

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